Preheat oven to 425°F (220°C). In saucepan, combine plums, brown sugar, vinegar, ginger, star anise, clove and cinnamon stick. Bring to a boil, then reduce to a simmer 30 min., or until thick and syrupy. Discard star anise, clove and cinnamon stick. Set plum chutney aside, keep warm.
In large bowl, mix butternut squash with 2 tbsp (30 mL) oil, 1 tsp (5 mL) salt and 1/2 tsp (2 mL) pepper to coat. Arrange in single layer on parchment-lined baking sheet. Roast squash 30 to 35 min., turning halfway, until golden brown and tender.
Meanwhile, season tenderloins with remaining salt and pepper. Heat remaining oil in large non-stick skillet over medium-high heat. Brown tenderloins on all sides, 4 to 6 min. Place on parchment-lined baking sheet. Cook in the preheated oven 15 to 17 min., or until an instant-read thermometer registers 160°F (71°C) when inserted into the thickest portion of the meat. Let stand 10 min. before slicing.
Served pork with plum chutney and roasted butternut squash on side.
Add pinch of hot pepper flakes to the chutney during simmering, if desired.